First Time to Santorini-3 Day Guide

My Post this week, First Time to Santorini-3 Day Guide, is a revision from an earlier post. As this was one of my first posts that I blogged I made some SEO and format changes. I also incorporated more informational links and maps. This 3 day guide follows our first trip to Santorini in September of 2018 and hits on some of the main attractions which was perfect. You can follow the links below for our 2019 trip to Santorini in which we explored the island in more detail. We also plan on returning again this September, 2021 as we really love the island and there is still more to see!

Day 1:

Arriving in Santorini

We arrived at the Port of Athinios in Santorini after a 2.5 hour Seajet ferry from Milos. Finding our transfer driver was no problem even though the port was crowded. We use the tour group, True Trips Greece. We have found them to be invaluable and also very knowledgeable.

Imerovigli

It didn’t take long to reach our hotel, Astra Suites which is located in Imerovigli. Imerovigli is between Fira and Oia, although closer to Fira. In addition, Imerovigli is much more quiet and less busy. Perfect for us. Our concierge showed us to our accommodations and also gave us a tour of the room. After that, he arranged a walking tour with a guide of Santorini for day 3 of our trip. He also reserved us a table at the Astra Suite Restaurant for the evening.

The Rock of Skaros

Barely settled in, we knew exactly where we wanted to go. The Rock of Skaros which was right in front of us! We wanted to enjoy a bit of adventure and climb this ancient fortress. The Rock of Skaros was formed by a volcano thousands of years ago. In addition, a fortress was built around the rock in the 14th century. Houses and buildings were also built around the rock for protection from raiders. In the 18th century, earthquakes reduced the fortress to rubble and ruins. As a matter of fact, these ruins are still present today.

Climbing the Rock

As hotel staff pointed the way, we followed their directions toward Fira and past a small church where we found the path and followed it. The trail was a bit rocky with lots of steps but the scenery beautiful. We passed by ruins of the old fortress and also had great views of the caldera and the blue sea. The path seemed to end towards the top because there was no particular pathway the last 20 feet or so. In reality, it was a vertical climb up which I decided not to climb, although Steve did and enjoyed the view.

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Sunset at the Astra Suites Restaurant

After exploring and a dip in the pool back at Astra Suites it was time for dinner. Dinner was at the Astra Suite Restaurant. The ambiance was second to none with the Rock of Skaros in front of us and also a beautiful sunset over the caldera. Our wait staff was attentive, the food was marvelous, and our first dinner in Santorini was perfect.

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Day 2:

Fira Town and Sailing Tour

We awoke early and enjoyed breakfast on our own terrace just outside our door. After breakfast we were ready to explore more of Santorini.

Town of Fira

We decided to spend the morning in Fira. It is a 1.4 mile walk from Imerovigli, where we were staying. You can also take the bus to Fira or a transport. You can also rent a car, ATV, or Dune Buggy. We found walking worked for us. The path to Fira takes you up and down many steps, past churches, restaurants, hotels, shops and more. It is quite the workout! Wandering around the narrow cobblestone streets is so much fun. Fira was busy, although not so crowded we couldn’t take pictures and enjoy a leisurely pace. We were there early in the morning which helps avoid the cruise ship tourists.

Sunset Sailing Tour

Next on our agenda was the Catamaran tour. Soon we were sailing over the turquoise waters of the Aegean Sea. We passed the Red Beach and the White Beach.

The crew also sailed us around the tiny island of Nea Kameni, just off the Santorini shore. Nea Kameni is still an active volcano and responsible for creating Santorini as it is today. You can take a boat ride there and climb to the top on some tours. The water is warmer here because of the volcano. I didn’t swim because it was too chilly for me, although Steve did enjoy a swim.

The crew prepared a delicious dinner. It was quite the feast. We dined on pork, shrimp, chicken, and several side dishes. The fava was so yummy. We sailed out to sea to view the sunset. Unfortunately, the evening’s sky was a bit overcast. Regardless, viewing the sunset from sea was still spectacular. Our boat tour ended as the sun went down.

Day 3:

Walking Tour

Today we were excited as we prepared to go on a walking tour of Santorini, complete with wine tasting! It was day 3 in Santorini and having a guide show us around the island was the perfect activity. After another great breakfast on our terrace, we walked up the many steps to the road to meet the tour guide and 3 other tourist couples. Blue Shades of Greece was the name of the tour company with Billy as our guide. Billy was knowledgeable and we liked him immediately.

Pyrgos

First stop was the charming village of Pyrgos. Pyrgos is set inland Santorini and is a peaceful village immersed in culture. Remnants of it’s medieval past are scattered throughout the town. Pyrgos hosts one of the 5 Venetian Fortresses in Santorini, which is Kasteli Pyrgos. When you roam the streets of Pyrgos you will see authentic Greek culture, not as touristy as you see in Fira and Oia, although there are some shops. It is also much less crowded. Billy led us around to the sites in town. He then led us atop a hill where we awed at a panoramic view of the Aegean Sea and Fira in the distance. Interesting to note, in 1953 there was an earthquake which did considerable damage to several of the structures and homes. Sadly, some have never been repaired.

Akoritori

I was excited about the next stop since it was on our must see list. Akortori is an ancient Minoan Civilization. It also was covered by a volcanic eruption in the 16th century BC. Reminiscent of Pompeii, volcanic ash buried the city which therefore preserved it. No human remains were found, unlike Pompeii, the people had some type of warning and evacuated. Excavation is still being performed. When you visit this ruin it is enclosed to protect the area. You are able to walk around platforms which overlook the ruins and excavation areas. You can also walk around on the ground floor amongst some of the ruins.

After viewing the ruins we took a short drive to Vilchada Beach, which is a black sand beach. We also passed a tomato factory and museum. I can’t imagine what is in a tomato museum but I wish I would have had the chance to find out!

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Megalochori

Megalochori, next on our agenda, is another picturesque village to explore on Santorini. Quiet and traditional like Pyrgos, Megalochori, has it’s own distinctive charm. Like Pyrgos, it is located inland, furthermore, the countryside around the little village is rich with vineyards. Interestingly, the vineyards in Santorini do not grow upward on trellises. As a matter of fact, the grape vines are close to the ground. Since ancient times and continuing today, the vines are trained to grow close to the ground, in a circle, resembling a basket or bowl, subsequently, preserving water for the plant.

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Venetsanos Winery

Speaking of grapes, next stop was the Venetsanos Winery. Located high on a cliff overlooking the sea, Venetsanos was a perfect place for a wine and food tasting. Five types of wine were sampled. In addition, local food was paired perfectly with each sampling of wine. Varieties of cheese, fava, pork, grape leaves, and tomato fritters were served. Tomato fritters are a must try Santorini specialty and Fava is also.

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Oia

Last stop, the beautiful, Oia. Billy expertly maneuvered us up steps and through alleys finding the best place to view the iconic Oia Blue Domes. Oia is similar to Fira, with shops and restaurants lined along the narrow cobblestone streets although much more busy.

We had never thought we would enjoy a walking tour as much as we enjoyed this one. That is to say, it was interesting and at each place we were able to get out and explore and we never felt rushed. Blue Shades of Greece showed us a comprehensive tour of Santorini and had us visiting places we would not have discovered on our own. Billy was an amazing tour guide he showed us great places and gave us awesome inside information! I highly recommend this tour!

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Dinner at Anogi, Imerovigli

Supper was at Anogi, a restaurant recommended by our tour guide. Anogi is walking distance from Astra Suites so this worked perfectly. Dinner was wonderful with souvlaki being my choice, whereas Steve again chose shrimp. I selected a local white wine which complemented my meal nicely.

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Another Walk to Fira

Steve wanted to walk back to Fira to buy a few T-shirts he had seen yesterday. I wasn’t fond of the idea because we had walked and climbed a lot of stairs today! Regardless I was glad I went! Fira was vibrant at night. All and all, there was a festive atmosphere as the lights were bright and music could be heard from tavernas and restaurants, many people were out and about. Steve found some T-shirts so we headed back. I was not enjoying the steps at all. Fortunately, a local told Steve of a back way with less steps. He found the area and we followed the alley back to Imerovigli, as a result, I was much happier. Thus ended our last night in Santorini.

Where We Stayed: Astra Suites

We stayed at the award winning Astra Suites both times when in Santorini and will stay there again this fall. All in all, Astra Suites is amazing! In addition, our room was located adjacent to the infinity pool which overlooked the caldera and the majestic Rock of Skaros. For more information on Astra Suites follow this link to their home page. Astra Suites.

Conclusion

I hope you enjoyed following our first trip to Santorini and you can use this 3 day guide as you plan your own trip! You can reference more things to do below on my links from our 2019 trip to Santorini. I can’t wait to return there this fall and post a more comprehensive guide of what to do, as we have a lot more to explore on this beautiful island!

Resources and Planning

Travel Agent

We use True Trips Greece as our Travel Agent. They were highly recommended to us by one of my husbands associates. This group is awesome and they are located in Greece so know all the ins and outs. They arranged all of our hotels, transfers (car, local air and ferry) and some of our activities once we arrived in Greece for our itinerary in Athens, Milos and Santorini. From picking us up at the airport the first day to getting us back at the end, everything went smoothly. Everyone was prompt, courteous and had great information! We used True Trips services for both our 2018 and 2019 trip. Currently we are working with them for our 2021 trip! They have been there for us and are keeping us informed through this entire Covid mess. I can’t say enough good things about this company.

Internet Information

• Greeka.com This site has so much useful information and is a great resource. I have checked out this site many times while trying to decide where to go in Greece.
• Santorini.com This site has great information on Santorini and the many villages on the island. Great background information. It also has a wealth of information on what to see and do.

For more on our 2018 and 2019 trip to Greece and Santorini you can follow these links:

Santorini by Dune Buggy Oct 2019

Our 5 Favorite Places to Eat in Santorini 2018 and 2019

Amoudi Bay in Santorini Oct 2019

Hike from Imerovigli to Oia Oct 2019

Path from Imerovigli to Fira Oct 2019

Astra Suites 2018 and 2019

10 Days in Greece 2019

8 Days in Greece 2018

Exploring Athens on a Rainy Day Sept 2018

3 Day Guide to Milos, Greece Sept 2018

5 Best Beaches in Milos Greece Sept 2018

Acropolis and Parthenon Sept 2018

Diary of a Gen-X recommendations for hotels and restaurants are based on our own experiences. We do not receive compensation for recommending at any of these nor are we affiliates of any hotels or restaurants. We only recommend restaurants that we have personally visited and we feel have great food and great service. The only hotels we recommend are again places we stayed which were clean, comfortable, and provided great hospitality.